Quantitative standards of 4-O acetyl and 9-O acetyl N-acetyl neuraminic acid for the analysis of plasma and serum

Cheeseman, J., Badia, C., Thomson, R. I., Kuhnle, G. ORCID: https://orcid.org/0000-0002-8081-8931, Gardner, R. A., Spencer, D. I. R. and Osborn, H. M. I. ORCID: https://orcid.org/0000-0002-0683-0457 (2022) Quantitative standards of 4-O acetyl and 9-O acetyl N-acetyl neuraminic acid for the analysis of plasma and serum. ChemBioChem, 23 (5). e202100662. ISSN 1439-7633 doi: 10.1002/cbic.202100662

Abstract/Summary

N-Acetyl neuraminic acid (sialic acid, Neu5Ac) is one of a large, diverse family of nine-carbon monosaccharides that play roles in many biological functions such as immune response. Neu5Ac has previously been identified as a potential biomarker for the presence and pathogenesis of cardiovascular disease (CVD), diabetes and cancer. More recent research has highlighted acetylated sialic acid derivatives, specifically Neu5,9Ac2, as biomarkers for oral and breast cancers, but advances in analysis have been hampered due to a lack of commercially available quantitative standards. We report here the synthesis of 9-O-acetyl and 4-O-acetyl sialic acids (Neu5,9Ac2 and Neu4,5Ac2) with optimisation of previously reported synthetic routes. Neu5,9Ac2 was synthesised in 1 step in 68% yield. Neu4,5Ac2 was synthesised in 4 steps in 39% overall yield. Synthesis was followed by analysis of these standards via quantitative NMR (QNMR). Their utilisation for the identification and quantification of specific acetylated sialic acid derivatives in biological samples is also demonstrated.

Item Type	Article
URI	https://reading-clone.eprints-hosting.org/id/eprint/101834
Identification Number/DOI	10.1002/cbic.202100662
Refereed	Yes
Divisions	Interdisciplinary centres and themes > Chemical Analysis Facility (CAF) Life Sciences > School of Chemistry, Food and Pharmacy > Department of Food and Nutritional Sciences > Human Nutrition Research Group Life Sciences > School of Chemistry, Food and Pharmacy > School of Pharmacy > Medicinal Chemistry Research Group
Publisher	Wiley
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